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Glucosyringic acid

Family: Plantae - Iridaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(OC)cc(cc2OC)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)/t9-,10-,11+,12-,15+/m1/s1
InChIKey	BLKMDORKRDACEI-OVKLUEDNSA-N
Formula	C₁₅H₂₀O₁₀
HBA	9
HBD	5
MW	360.31
Rotatable Bonds	6
TPSA	155.14
LogP	-1.42
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	360.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Iris spuria	Iridaceae	Plantae	93026

Showing of synonyms

Farag SF, Kimura Y, et al. (2009). New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. Journal of Natural Medicines,2009,63(1),91-95. [View] [PubMed]

Pubchem: 10383888

Cas: 33228-65-8

Zinc: ZINC000038697541

Nmrshiftdb2: 60021862

Chembl: CHEMBL5082798

Comptox: DTXSID20186870

No compound-protein relationship available.

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 360.31 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 360.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 360.31 g/mol

Antiviral

Absorption

Caco-2 (logPapp): -6.08
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.050
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 71.08
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.540
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.290
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.220
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.430
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -1.450
Rat (Acute): 1.780
Rat (Chronic Oral): 3.910
Fathead Minnow: 3.860
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 449.020
Hydration Free Energy: -17.760
Log(D) at pH=7.4: -1.890
Log(P): -0.95
Log S: -1.94
Log(Vapor Pressure): -11.08
Melting Point: 176.06
pKa Acid: 3.75
pKa Basic: 4.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8790
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8790
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.7921
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.7921
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7898
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7898
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7684
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7684
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7617
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7617
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7407
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7407
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7288
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7288
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7264
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7264
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.7175
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.7175
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7104
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7104
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7096
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7096
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7067
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7067
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7024
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7024
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7009
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7009

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